The experiences of care of people with lived experience of homelessness are rarely embraced to change care delivery. We conducted qualitative group and one-on-one interviews utilizing experience group methodology with 27 people with lived experience of homelessness currently housed in one permanent housing community in central Texas. We analyzed data using an inductive thematic approach to identify shared obstacles and barriers to receiving health care. We then analyzed findings with the capability, comfort, and calm value framework to identify health outcomes that matter most to study participants. Poor access to care, discontinuities in care, distrust in providers, and confusing terminology were identified as the biggest barriers to health. The overwhelming majority of experiences reflected poor health outcomes of calm, the outcome of a health care experience that adds ease to one’s life rather than logistical and administrative chaos. We propose three practical approaches to achieve calm for this population as follows: systems-level embracement of compassionate care, integration of relationship-based care navigation into all levels of care, and building efficient transportation into care design. We conclude that designing health care that works in the lives of people with lived experience of homelessness is critical to address the gaps in care that fuel the health disparity these individuals face compared to people without this lived experience.